5-tert-butylpyridine-2-carboxylic acid methyl ester | 215436-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-tert-butylpyridine-2-carboxylic acid methyl ester
• 英文别名: methyl 5-tert-butylpyridine-2-carboxylate；methyl 4-tert-butyl-2-picolinate；methyl 5-(tert-butyl)picolinate；5-tert-butyl-pyridine-2-carboxylic acid methyl ester
• CAS: 215436-29-6
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: JRXBWYKPWHPFQO-UHFFFAOYSA-N

物化性质

• 沸点：
  289.4±28.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-tert-butylpyridine-2-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-叔丁基吡啶-2-甲醛
  参考文献：
  名称：

  Discovery of Potent, Orally Available Vanilloid Receptor-1 Antagonists. Structure−Activity Relationship of N-Aryl Cinnamides

  摘要：

  The vanilloid receptor-1 (TRPV1 or VR1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role in regulating the function of sensory nerves. A growing body of evidence demonstrates the therapeutic potential of TRPV1 modulators: particularly in the management of pain. As a result of our screening efforts, we identified (E)-3-(4-tert-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (1): an antagonist that blocks the capsaicin-induced and pH-induced uptake of Ca-45(2+) in TRPV1-expressing Chinese hamster ovary cells with IC50 values of 17 +/- 5 and 150 +/- 80 nM, respectively. In this report.. we describe the synthesis and structure-activity relationship of a series of N-aryl cinnamides, the most potent of which (49a and 49b) exhibit good oral bioavailability in rats (F-oral = 39% and 17%. respectively).

  DOI：

  10.1021/jm049485i
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 3-tert-butyl-9,9-dimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester 在 N-氯代丁二酰亚胺 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-tert-butylpyridine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  PREPARATION OF SUBSTITUTED PYRIDINES VIA REGIOCONTROLLED [4 + 2] CYCLOADDITIONS OF OXIMINOSULFONATES: METHYL 5-METHYLPYRIDINE-2-CARBOXYLATE

  摘要：

  DOI：

  10.15227/orgsyn.080.0133

文献信息

• TRICYCLIC GYRASE INHIBITORS
  申请人：Bensen Daniel

  公开号：US20120238751A1

  公开（公告）日：2012-09-20

  Disclosed herein are compounds having the structure of Formula I and pharmaceutically suitable salts, esters, and prodrugs thereof that are useful as antibacterially effective tricyclic gyrase inhibitors. Related pharmaceutical compositions, uses and methods of making the compounds are also contemplated.

  本文披露了具有式I结构的化合物，以及作为抗菌有效的三环酶抑制剂的药用盐、酯和前药，相关的药物组合物、用途和制备该化合物的方法也在考虑之中。
• HETEROARYL COMPOUNDS AS BTK INHIBITORS AND USES THEREOF
  申请人：Merck Patent GmbH

  公开号：US20160096834A1

  公开（公告）日：2016-04-07

  The present invention relates to imidazo pyridine compounds, and pharmaceutically acceptable compositions thereof, useful as BTK inhibitors.

  本发明涉及咪唑吡啶化合物及其药学上可接受的组合物，用作BTK抑制剂。
• Aromatic Ring Cleavage of 2-Amino-4-<i>tert</i>-butylphenol by a Nonheme Iron(II) Complex: Functional Model of 2-Aminophenol Dioxygenases
  作者：Biswarup Chakraborty、Tapan Kanti Paine

  DOI：10.1002/anie.201206922

  日期：2013.1.14

  Biomimetic aromatic ring cleavage: An iron(II)‐2‐aminophenolate complex (see picture, right) with a tetradentate ligand reacts with dioxygen to cleave the aromatic CC bond of 2‐amino‐4‐tert‐butylphenolate to form 4‐tert‐butyl‐2‐picolinate. This complex represents a functional model of 2‐aminophenol‐1,6‐dioxygenase (APD) and 3‐hydroxyanthranilate‐3,4‐dioxygenase (HAD).

  仿生芳香环裂解：具有四齿配体的铁（II）-2-氨基酚盐络合物（见右图）与双氧反应，裂解2-氨基-4-叔丁基酚盐的芳族CC键，形成4- 2-吡啶甲酸叔丁酯。该复合物代表了2-氨基苯酚-1,6-二加氧酶（APD）和3-羟基邻氨基苯甲酸酯-3-3,4-二加氧酶（HAD）的功能模型。
• Heteroaryl and benzyl amide compounds
  申请人：Faeh Christoph

  公开号：US20070185113A1

  公开（公告）日：2007-08-09

  Compounds of formula I processes for their preparation, their use as pharmaceuticals and to pharmaceutical compositions comprising them.

  公式I化合物的制备方法，以及它们作为药物的用途和包含它们的药物组合物。
• Development of an Iron(II)-Catalyzed Aerobic Catechol Cleavage and Biomimetic Synthesis of Betanidin
  作者：Nicolas Guimond、Peter Mayer、Dirk Trauner

  DOI：10.1002/chem.201403436

  日期：2014.7.28

  An aerobic iron(II)‐catalyzed cleavage of catechols was developed. This reaction allows for the preparation of 2‐methoxy‐2 H‐pyrans that can be employed as versatile building blocks for synthesis. The utility of this biomimetic oxidative cleavage is featured in the synthesis of betanidin, a natural colorant with antioxidant properties.

  开发了好氧铁（II）催化的邻苯二酚裂解。该反应可制备2-甲氧基-2  H-吡喃，可用作合成的通用结构单元。这种仿生的氧化裂解的效用是甜菜碱合成的特征，甜菜碱是一种具有抗氧化性能的天然着色剂。